Screw Start With Why: The Problem With Internet Advice

Every single morning, I wade my way through about twelve trillion emails, a waist-high pool of LinkedIn posts and my RSS feed reader (yes! In 2024). Like everyone else, I’m all about upping my game and real-life advice from articles, newsletters, podcasts, books, grafitti art and kalidopscopes makes that happen. We all do it - we swarm to ideas like flies to a melted vanilla ice cream puddle. And it almost all lacks context.

We read them. We believe them. And then we start to evangelize them too.

We quote Sinek’s Start with Why and hunt for a mission so that, we too, can challenge the status quo (Apple) or democratize air travel (Southwest).

We talk about our next campaigns, creating our own “Just Do It” after reading Shoe Dog. We push our marketing team to create new categories after hearing about Hubspot’s Inbound Marketing or Gong’s Conversational Intelligence success. We cite encyclopedias of one-liners and examples, growth hacks, and tutorials with confidence that they worked.

(They probably did.)

The interviews pull us in even more. Founders ooze with credibility. Zuckerberg drops a “Move fast and break things” in a 2010 interview, and you need to hold yourself back from breaking stuff. Someone mentions Reid Hoffmann’s “If you’re not embarrassed by the first version of your product, you’ve launched too late," and you can’t stop thinking about a product you have that you need to launch already, goddammit.

Wake us up in the middle of the night and we’ll talk about NPS scores, Clay + deanonymizer tech stack playbooks for nurturing, and LinkedIn advertising recipes we read.

This is literally what memes are! These ideas spread faster than kat memes on Reddit, are less cute and are potentially downright damanging to your business.

The ideas may be right… but they aren't right for everyone or at everytime. And no one tells us that!

Leafblowers are great for when you want to clean your garden but terrible for when you are pruning roses (ask my sad, naked rose bush how I know). What is nothing without when and where. But the advice you read online rarely includes context on the tin. all advice is contextual. It worked for someone at some time. And the context you’re in is unlikely to replicate the context where it did work.

So screw those ideas… occasionally.

• Forget “Start with Why” when you shouldn’t start with why.
• Stop moving fast when you want to be more methodical.
• Don’t ship that MVP when it’s not VP enough.
• Be a little less customer-obsessed if it’s endangering your business.

The simplicity and repeatability of these ideas obscure the most important caveat— advice, frameworks, and tutorials are contextual. Knowledge, however elegant the prose, is only relevant when you know when to listen to them.

So why do they resonate with us so damn much?

These ideas speak to our inner cry for order.

Life is confusing and we’re all dealing with the s^$tstorm that is work.

Imagine you just started a job as a marketer at a new B2B tech company. You’re being leaned on to bring in All The Leads, to nurture those leads, and to build a billion dollar brand. It’s chaos and there aren’t enough hours in the day.

And then the skies open and 24 iridescent white doves fly out with a scroll of a LinkedIn post titled “How TrendyBrandName Scaled to $2.34m in pipeline with a trendy Swedish illustrator, $2.34 of LinkedIn spend, 15 home delivered kits of potter to select founders and an AI email cadence written by an ex-Bell Labs founder.”

It’s an instruction manual to tame the chaos. Obviously you’re going to grab it with both hands and pull.

The shorter ones are even more appealing. A one line guide for becoming as big as Your Hero. And it’s said with so much confidence!

So advice along the lines of “Don’t build links. Build relationships.” (Rand Fishkin) or “Outbound sales is a numbers game, but personalization gives you the edge." (Aaron Ross) feels like a law that you implicitly project right onto whatever reality you’re living.

This isn’t Zuck’s fault. He’s allowed to talk about moving fast and breaking things. It’s our fault for taking advice without recognizing that the ideas aren’t always:

• Good for your context
• Relevant for your context
• Possible in your context

As a small example, Rand Fishkin’s building relationships instead of links checks out but only when you don’t have easy access to high-ranking sites, in which case you should build the heck out of those links (despite the fact that it’s destroying the internet).

If you’re talking to someone who deeply knows your industry, your company, and your competitors, and all they want to talk about is features, you can try to push your story or push your capabilities, ala Fletch, but you risk losing them.

Internet Grapevine Makes It Worse

PSA: In many cases, the person providing the advice actually did provide the context…but the Internet Machine systematically spread the one-liner without the context. The end result is the same, with the exception that you shouldn’t egg the person who’s quoted.

Here’s proof.

The people who share ideas themselves acknowledge that they are not sacred cows and that some of their ideas should be made into hamburger meat.

Talking (and walking back) advice he gave while running YC about not raising too much and shipping fast, Sam Altman of now OpenAI fame said:

“Honestly, I feel so bad about the advice I gave while running YC I’ve been thinking about deleting my entire blog.”

– Via Twitter/X

Ten years into Facebook, Mark Zuckerberg downgraded “Move fast and break things” into a slightly less pithy “Move fast with stable infra."

And over ten years after saying it, Reid Hoffmann clarified that being embarrassed about what you launch doesn’t mean cutting corners or proceeding without a plan.

Again, I don’t hold these changes against them. We can’t expect one-liners to solve for infinite realities!

When (and how) to use internet advice.

Here’s the short of it:

• Consume content wisely. People who claim to know everything certainly do not.
• Spend at least as much time understanding your context.
• Understand your context: What works for a $100bn company might not work for you.
• . Test. Try everything that could work. Learn what works in which context.

Build up your pattern recognition skill

If there’s one part of that that I think has been most helpful (and has been the hardest to learn), it’s spending the time figuring out what applies to you. Because that pattern recognition is what allows a consultant to come in and slam it out of the park in the first 30 minutes.

Take into account factors like:

• Who said it. Where was the founder or expert when they said their line? Was their company venture backed? What was their funding like? Did they have the conviction to go big on it before they became big? What was their team like? Did they always walk the walk with that line? For instance, when companies blindly adopt the ‘move fast and break things’ mantra, they often overlook the specific conditions that made it work for Facebook—a massive user base and deep pockets to fix what broke.
• Your company’s strategy, goals and capabilities. Do you have the resources to pull it off? Maybe you can ship fast but can your QA team? Can your legal team? Can you maintain the quality that you want? Do you have the same 25k email list that a celebrity marketer had when he started his new product from scratch?
• The veracity of the statement. One-liners get appropriated, authors get creative about reading strategy from tactics with overly-attuned pattern recognition, and third-party case studies are just as often absolute junk. I once read a confidently written analysis about something my company did that had nothing to do with what we actually did.
• The specific problem you’re trying to solve. A playbook you read for a new design language may be interesting but if you don’t need it, it’s irrelevant.

Once you start asking questions about context, you’ll start building up your pattern recognition muscle. And that’s exactly what’ll make you an expert!

It works in chess too. A famous chess experiment by Adrian de Groot way back in the 1940s found that chess masters could look at a board for 3-4 seconds and recall the position of every piece with 93% accuracy. Grandmasters were masters at solving problems because they could understand a wide range of situations.

In other words, expertise isn't about being able to implement a playbook; it's about being able to identify a situation, diagnose it, and find the right piece of knowledge to solve it.

Take these “rules”—whether they’re about deep work (Cal Newport), learning quickly from experimentation (Sean Ellis), or any other strategy—as tools in your toolkit, not one-size-fits-all solutions. Otherwise you end up implementing the right advice in the wrong place, which is like playing chess with Monopoly advice and finding yourself building hotels on E4.

Then experiment.

If a plumber says to use a monkey wrench, he or she likely knows not to use them on plastics that can be damaged from the grip. But you don’t know that. That context matters, and you’ll need to figure out yourself when it works.

When you know that your own context can override rules, it shapes how you take advice. If you come across advice from a tailor telling you how to hem your pants, he might not know that you’re running out to a last-minute meeting and don’t have a second. If he did, he might have recommended doing what my grandfather used to do—hem his pants by stapling them (true story!).

The order the rules and playbooks create is real. But without knowing when to use each, you're back to chaos.

Outro

In a world drowning in advice, the real challenge isn’t finding what to do—it’s understanding when and how to do it. Context is the key to turning generic advice into actionable insight.

So next time you’re wading through your morning deluge of advice, remember: it’s not about what you read—it’s about how you apply it. So yes, collect the aphorisms.

But then recognize that they are only valuable when you start to explore. When you tinker with the tools you’ve been handed, find out what works and when, and learn what should be ignored.

Get your hands dirty.

See when influencer marketing works, when cold outbound works, and when brand investment works. If a monkey wrench works for you while someone else swears by a crescent wrench, that’s okay. Hell, if you can make it work with a pencil and a shoestring, more power to you.

Don’t let anyone—including me—tell you how to run your business. Consume the advice with vim and vigor. Build up your toolkit…but then learn how to use it yourself.